How can you add instant style this season? Easy—just pop on a Baker Boy hat. We’ve fallen in love with this hat style for its timeless appeal and the way it adds flair to any look. So, how can you wear a Baker Boy hat to elevate all your outfits? Let’s take a look.

What is a baker boy hat?

Before we get onto how to wear one, what exactly do we mean by a baker boy hat? Well, rather than a flat cap, or a baseball cap, the baker boy cap is more rounded and elevated, giving it more height and shape. You can also look for newsboy, breton, fisherman and fiddler caps, which also have that very similar raised crown look.

Sylvia in a striped shirt and black pants | 40plusstyle.com

similar shirt (another option here), wide pants, sneakers, hat, earrings and sunglasses

Why we love them

They are menswear inspired

Because baker boy hats take their inspiration from menswear, they immediately add a touch of the unexpected to your outfit.

They elevate simple outfits

You don’t have to think too much about the rest of your outfit because the hat adds style for you. Even if you’re wearing the simplest of looks like your favorite jeans and t-shirt, a baker boy hat instantly elevates your style and adds a talking point.

They’re a conversation starter

We bet you get lots of people telling you they like your hat. They’re a conversation starter and make you feel more confident.

You’re in good company

You’re also in great company when you wear a baker boy. While she isn’t quite in the 40+ bracket yet, we’ve spotted Blake Lively often wears a baker boy, as does Janelle Monae, and Katie Holmes.

Psyche in green coords | 40plusstyle.com

Psyche @economyofstyle above tops off her green co-ord outfit with a rattan baker boy hat, and matches her headwear to her sandals.

Recreate her outfit with this similar green coordinates, sandals, hat and belt.

The best baker boy hats in stores now

Let’s show you some examples of the most stylish baker boy hats you could choose in stores.

For a true classic, opt for a gray felt baker boy like the Isabel Marant cap (below).

Isabel Marant Evie Wool-Blend Newsboy Cap | 40plusstyle.com

Isabel Marant Evie Wool-Blend Newsboy Cap

The Eugenia Kim cap (below) features a little bit of bling thanks to the chain detailing.

Green baker boy cap | 40plusstyle.com

Eugenia Kim Sabrina Wool Newsboy Cap

If you have a glamorous style personality, then the sparkly baker boy (below) is for you. Keep the rest of your outfit pretty simple.

Ruslan Baginskiy Embellished Baker Boy Cap | 40plusstyle.com

Ruslan Baginskiy Embellished Baker Boy Cap

Mixing black and white is always timeless and the monochrome cap (below) has done this for you. You might want to add this to one of your black and white outfits.

Ruslan Baginskiy Baker Boy Cap | 40plusstyle.com

Ruslan Baginskiy Baker Boy Cap

You can wear baker boys for any season. Choosing a linen blend like the MANGO cap (below) can be a great way to wear your cap into the warmer months.

MANGO Linen-Blend Baker Boy Cap | 40plusstyle.com

MANGO Linen-Blend Baker Boy Cap

Add a pop of color to your outfits with the red cap (below).

CRAGGIHATS Berker Boy Hat | 40plusstyle.com

CRAGGIHATS Berker Boy Hat

A hat can also be a great way to add texture to your outfit like to cord cap (below) with button detail.

accsa Newsboy Cap | 40plusstyle.com

accsa Newsboy Cap

Checks are a fantastic print for a baker boy cap. We love the herringbone print on the hat below.

Comhats Merino Newsboy Hat | 40plusstyle.com

Comhats Merino Newsboy Hat

Or, opt for a bolder, more colorful check like the newsboy (below).

Hatful Memories Newboy Cap | 40plusstyle.com

Hatful Memories Newsboy Cap

Another option with a chain for you now, this time in a stylish black print.

INOGIH Baker Boy Hat | 40plusstyle.com

INOGIH Baker Boy Hat

Outfit ideas for your baker boy hat

So, now that you’ve picked out your favorite baker boy, what should you wear it with? Let’s take a look.

With your favorite jeans

A great starting point for your outfit is to pick out your favorite pair of jeans, and your hat. Then, simply add a T-shirt or blouse and you’re good to go. Below, we’ve chosen to mix the masculine nature of the hat with a feminine blouse. For cohesion, we’ve matched the handbag color to the cap.

Jeans and baker boy outfit | 40plusstyle.com

Alice + Olivia April Floral Blouson-Sleeve Top – Alice + Olivia Missa Crystal Stripe Wide-Leg Jeans – LAUREN Ralph Lauren Leona Espadrille Sandals – Aimee Kestenberg Aura A-Line Shoulder Bag – Kendra Scott Chandlier Huggie Earrings – Eugenia Kim Sabrina Wool Newsboy Cap

Eileen in a baker boy hat and striped sweater | 40plusstyle.com

Eileen @eileenternullo above opts for a maritime inspired outfit with her cap and striped sweater.

Get her look with this similar sweater, jeans, sneakers, hat, earrings and sunglasses.

With cargo pants

Cargo pants are particularly on trend this season and go really well with baker boy hats. Wear with a camisole and denim jacket.

Cargo pants and denim jacket outfit | 40plusstyle.com

Ronny Kobo June Denim Jacket – Theory Animal-Print Jacquard Tank – Alice + Olivia Olympia Mr Baggy Cargo Pants – Franco Sarto Diva Kitten Heel Pumps – Aimee Kestenberg Aura A-Line Shoulder Bag – LAUREN Ralph Lauren Tartan Hoop Earrings – Isabel Marant Evie Wool-Blend Newsboy Cap

With sailor pants

Sailor pants are another great pairing for baker boy hats. Below, we’ve also added a sleeveless trench coat.

Trench coat and sailor pants outfit | 40plusstyle.com

J.Crew Étienne Oversized Shirt – COS Sleeveless Trench Coat (similar here) – Alice + Olivia Narin High-Rise Stretch Flare Crop Jeans – Bzees Everly Strappy Sandals – Cole Haan Go Anywhere Tote – Shashi Hailey Drop Earrings – Hatful Memories Newboy Cap

with black pants and a graphic print top

Black pants are a classic that go with everything, including your baker boy caps. For added drama, wear with a graphic print sweater.

Graphic print top and black pants outfit | 40plusstyle.com

Alice + Olivia Oscar Saceface Double Knit Pullover Sweater – Alice + Olivia RMP Back Zip Bootcut Pants – Söfft Carleigh Heeled Sandals – Madewell Soft Grain Shopper – LAUREN Ralph Lauren Tartan Hoop Earrings – CRAGGIHATS Berker Boy Hat

Fonda wears a baker boy hat | 40plusstyle.com

Fonda @savvysouthernchic above keeps the rest of her outfit simple and elevates her style with her baker boy hat.

Steal her look with this similar sweater, jeans, boots, hat, earrings and necklace.

with Blazer dress and slim pants

For a glamorous evening look, wear your baker boy hat with a blazer dress and slim pants.

Baker boy hat and blazer outfit | 40plusstyle.com

Alice + Olivia Esther Embellished Cotton Blazer Dress – BOSS Slim-Fit Jeans in Comfort-Stretch Denim – Franco Sarto Diva Kitten Heel Pumps – Cole Haan Go Anywhere Tote – Shashi Hailey Drop Earrings – INOGIH Baker Boy Hat

with ruana

A great look for transitional weather, pair your baker boy with a ruana or poncho.

Ruana and baker boy hat outfit | 40plusstyle.com

UGG Tasman Ruana – Misook V-Neck Soft Knit Tank Top – Good American Good Legs Crop Skinny Jeans – Anne Klein Suri Suede Boots – Madewell Soft Grain Shopper – COS Organic-Shaped Pendant Necklace – Comhats Merino Newsboy Hat

With a sleeveless dress and t-shirt

Do you have a sleeveless dress in your closet? Update it by wearing it layered with a t-shirt underneath, and top off with your cap.

Striped t-shirt and dress outfit | 40plusstyle.com

Theory Boxy Striped T-Shirt – Staud Ellison Knit Pleated Midi-Dress – Tory Burch Howell Court Sneakers – Cole Haan Go Anywhere Tote – Kendra Scott Chandlier Huggie Earrings – Ruslan Baginskiy Baker Boy Cap

Sylvia in a sleeveless dress and baker boy hat | 40plusstyle.com

similar tee, dress (another option here), tights, boots, bag (another option here), earrings, hat and sunglasses

With maxi skirt

A maxi skirt is a great way to add drama to casual looks, and you can up the style stakes by adding a baker boy cap.

Maxi skirt and cable knit sweater | 40plusstyle.com

Polo Ralph Lauren Julianna Cashmere Cable-Knit Sweater – Alice + Olivia Rye Tweed Slit Maxi Skirt – Söfft Carleigh Heeled Sandals – Madewell Soft Grain Shopper – LAUREN Ralph Lauren Tartan Hoop Earrings – accsa Newsboy Cap

with full skirt

For a preppy take on the baker boy trend, wear with a polo neck top and full skirt.

Polo neck top and full skirt | 40plusstyle.com

J.Crew Vintage Rib Polo T-Shirt – Alice + Olivia Earla Lace Midi-Skirt – Tory Burch Howell Court Sneakers – Madewell Soft Grain Shopper – LAUREN Ralph Lauren Tartan Hoop Earrings – MANGO Linen-Blend Baker Boy Cap

Your baker boy cap outfits together in one capsule

How to wear this season's trendiest hat: the baker boy hat | 40plusstyle.com

similar dress (other options here, here and here), sandals, hat, earrings, necklace, sunglasses, backpack

Below, you can see the outfits from above together in one capsule. You can see you can wear the clothes, shoes and accessories in different ways to create many more looks.

Baker boy hat outfits | 40plusstyle.com

shop the outfits and baker boy hats below:

Has this article inspired you to add a Baker Boy cap to your closet and your outfits? Or are you already wearing one? Let us know in the comments below.

Continue reading:

  1. 10 Essential Fashion Accessories Every Woman Should Own
  2. How To Wear A Hat – The Ultimate Guide
  3. The Best Shops On Etsy And Other Brands For Contemporary Jewelry

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How to wear this season's trendiest hat: the baker boy hat | 40plusstyle.com

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